As a youth, Middleton played in the 1966 Quebec International Pee-Wee Hockey Tournament with a minor ice hockey team from Wexford, Toronto.\n', '

A right winger, Middleton was drafted in the first round, 14th overall, by the Rangers in the 1973 NHL Amateur Draft after a glittering junior career with the Oshawa Generals in which he led his league in scoring his final year and was named to the league\'s Second All-Star Team. He spent the 1973–74 season with the Rangers\' farm team, the AHL Providence Reds, earning rookie of the year honors and being named to the AHL\'s First All-Star Team.\n', '

He made the big club during the 1974–75 season, and despite suffering injuries that restricted him to 47 games, scored 22 goals in that limited time. The following season was not as spectacular, as he scored 24 goals in 77 games while showing defensive deficiencies.\n', '

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